WO2023179870A1 - 4-oxopentanoate d'éthyle pour réduire les odeurs - Google Patents

4-oxopentanoate d'éthyle pour réduire les odeurs Download PDF

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Publication number
WO2023179870A1
WO2023179870A1 PCT/EP2022/057929 EP2022057929W WO2023179870A1 WO 2023179870 A1 WO2023179870 A1 WO 2023179870A1 EP 2022057929 W EP2022057929 W EP 2022057929W WO 2023179870 A1 WO2023179870 A1 WO 2023179870A1
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Prior art keywords
ethyl
oxopentanoate
odor
methyl
acetate
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PCT/EP2022/057929
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English (en)
Inventor
Vijayanand CHANDRASEKARAN
Bernd HÖLSCHER
Original Assignee
Symrise Ag
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Publication date
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Priority to PCT/EP2022/057929 priority Critical patent/WO2023179870A1/fr
Publication of WO2023179870A1 publication Critical patent/WO2023179870A1/fr

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11B—PRODUCING, e.g. BY PRESSING RAW MATERIALS OR BY EXTRACTION FROM WASTE MATERIALS, REFINING OR PRESERVING FATS, FATTY SUBSTANCES, e.g. LANOLIN, FATTY OILS OR WAXES; ESSENTIAL OILS; PERFUMES
    • C11B9/00—Essential oils; Perfumes
    • C11B9/0007—Aliphatic compounds
    • C11B9/0015—Aliphatic compounds containing oxygen as the only heteroatom
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
    • A61K8/37—Esters of carboxylic acids
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
    • A61L9/00—Disinfection, sterilisation or deodorisation of air
    • A61L9/01—Deodorant compositions
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q13/00—Formulations or additives for perfume preparations
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q15/00—Anti-perspirants or body deodorants
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
    • A61L2101/00—Chemical composition of materials used in disinfecting, sterilising or deodorising
    • A61L2101/32—Organic compounds

Definitions

  • the present invention relates to the use of Ethyl 4-oxopentanoate for reducing odors or as an auxiliary agent for reducing odors.
  • Ethyl 4-oxopentanoate to be used according to the invention may be present in any stereoisomeric form or may be present as any mixture of stereoisomers.
  • Reduction of odors is used in the present text to mean partial reduction or total reduction, i.e. elimination of odors, in particular unpleasant odors by a specific substance.
  • Unpleasant odors in the sense of the present invention are in particular odors of human sweat, human faecal or urine, kitchen odors, in particular odors of old fat, old fish or butyric acid, and smoke or similar type of odors.
  • a scenting or perfuming of a product in the narrower sense is to be distinguished from a neutralization or reduction of an unpleasant odor and can occur in addition to such a neutralization/reduction. Scenting or perfuming is understood to mean imparting an olfactory impression, i.e. an additional olfactory effect which may go beyond a complete or partial reduction of the unpleasant odor.
  • a fragrance is, in the broader sense, any substance that causes an olfactory impression or changes the olfactory perception of another substance due to an inherent odor.
  • a fragrance is a substance that produces an olfactory impression, in particular an olfactory impression in humans.
  • a fragrance mixture is a mixture comprising at least one, but in particular two or more fragrances in the narrower or broader sense.
  • the odor to be reduced according to the invention is preferably an unpleasant odor.
  • unpleasant odors affect people's well-being.
  • Such an unpleasant odor is preferably an odor of human exhalations and excretions, especially sweat, faeces and urine odors, i.e. in particular a human body odor, very particularly a human sweat odor (especially armpit sweat odor), or an odor of faeces or urine of animals, especially pets, or an odor of wet animal fur, especially wet fur of dogs or sheep, an odor of wet sheep's wool, or kitchen odors such as e.g. B.
  • such an unpleasant odor is toilet odor, especially human faeces and urine odors, odors of faeces or urine of animals, especially pets, kitchen odors, especially old fat, old fish or butyric acid, or smoke, especially (cold) tobacco smoke.
  • odors that are preferably to be reduced in the context of the use according to the invention are unpleasant odors of industrially produced raw materials that are used in cosmetic, body care, household or cleaning products.
  • an unpleasant odor can be an odor that occurs when using special cosmetic preparations such as e.g. hair coloring, hair shaping and depilatory products.
  • Ethyl 4-oxopentanoate to be used according to the invention is advantageously light accessible or producible, has a high effectiveness even at low concentrations, especially at concentrations at which Ethyl 4-oxopentanoate has no or at least only a barely perceptible odor, is largely or completely colorless, has a high stability in different mixtures or preparations and does not have any toxic and/or allergenic effects on humans.
  • Ethyl 4-oxopentanoate has the advantage that when used, in particular when used according to the invention, it can be combined with different fragrances and perfume oils or customary components of a perfume oil in order to perfume products with any desired fragrance. Consequently, a wide range of fragrance types can be offered to consumers by the present invention.
  • Perfume mixtures and perfumed products according to the invention containing Ethyl 4-oxopentanoate are described below.
  • Ethyl 4-oxopentanoate is renewable and bio-degradable, which is one of the most important things for the future fragrance industry.
  • Ethyl 4-oxopentanoate is not yet known as a fragrance compound; therefore, no precise odor description is already available.
  • Ethyl 4- oxopentanoate to be used according to the invention only has a very faint intrinsic odor.
  • the odor, preferably the unpleasant odor, to be reduced is thus primarily not masked by a specific intrinsic odor of Ethyl 4-oxopentanoate in question. It is true that the mechanisms of action of the odor neutralization/odor reduction taking place within the scope of the present invention have not yet been conclusively clarified.
  • Ethyl 4-oxopentanoate to be used according to the invention interacts with various receptors in the olfactory mucosa of the human nose, which presumably leads to an (olfactory) sensory illusion, so that the perceived olfactory impression is no longer associated with the original cause (an unpleasant smell).
  • the intrinsic odor of Ethyl 4-oxopentanoate to be used according to the invention is preferably so weak or of such low (odor) intensity that it can hardly be perceived (by humans). This (very weakly smelling) Ethyl 4-oxopentanoate is to be regarded as (perfume) auxiliaries for the purposes of the present invention.
  • Ethyl 4-oxopentanoate to be used according to the invention or corresponding mixtures to be used according to the invention are particularly suitable for reducing an odor, in particular an unpleasant odor (e.g. in corresponding odor neutralized or scented products), and / or as an adjuvant to reduce an (unpleasant) odor.
  • Ethyl 4-oxopentanoate also has the advantage that when it is used, in particular when it is used according to the invention, it can be combined with a wide variety of fragrances and perfume oils in order to perfume objects or products, in particular those with unpleasant odors, with any desired fragrance or to scent. [0021] Consequently, the present invention allows a wide range of fragrance types to be offered to consumers in combating unpleasant odors.
  • Ethyl 4-oxopentanoate has the following characteristics:
  • Ethyl 4-oxopentanoate has a molecular weight of 144.08 g/mol and a molecular formula of C7H12O3.
  • Ethyl 4-oxopentanoate has the following CAS-No.: 539-88-8. Furthermore, Ethyl 4-oxopentanoate is also known as Ethyl levulinate.
  • Ethyl 4-oxopentanoate is used together with one or more fragrances different from Ethyl 4-oxopentanoate for reducing odors or as an auxiliary agent for reducing odors.
  • this can result
  • the unpleasant odor is preferably selected from the group consisting of sweat, in particular human sweat, toilet odor, human faecal or urine odor, odors from faecal or urine from animals, kitchen odors, in particular odors of old fat, old fish or butyric acid, and smoke odor, in particular of cold smoke odor.
  • Ethyl 4-oxopentanoate is used together with at least one fragrance different from Ethyl 4-oxopentanoate for reducing odors.
  • the at least one fragrance different from Ethyl 4-oxopentanoate is preferably selected from the group consisting of Alpha-hexyl cinnamon aldehyde, 2- phenoxyethylisobutyrate, dihydromyrcenol, methyl-dihydrojasmonate, 4,6,6,7,8,8,- hexamethyl-1,3,4,6,7,8-hexahydrocyclopenta[g]benzopyran, tetrahydrolinalool, benzyl acetate, 2-methyl-3-(4-tert.-butyl-phenyl)propanal, cinnamon alcohol, 1 -phenyl acetate, octahydro-2,3,8,8,-tetramethyl-2-acetophenone, 2-acetyl-1,2,3,4,6,7,8- octahydro-2,3,8,8-tetramethyl naphthalene, 4-tert.-butylcyclohexyl-acetate,
  • the ratio of the total amount of Ethyl 4-oxopentanoate to the total amount of fragrances by weight is in the range from 10: 1 to 1 : 50, preferably in the range from 5: 1 to 1 : 30, particularly preferably in the range from 2:1 to 1 :20, particularly preferably in the range from 3:2 to 1 :10.
  • Ethyl 4-oxopentanoate can be used in a variety of products; it can be used as a single fragrance, but it can be combined particularly advantageously with other fragrances in different proportions to form fragrance mixtures, and novel and original perfume compositions can also be created. Accordingly, one aspect of the invention also relates to a fragrance mixture and possibly further constituents (solvents or the like), which contains Ethyl 4-oxopentanoate.
  • the fragrance composition according to the invention comprises or consists of Ethyl 4-oxopentanoate and one or more, preferably two, three, four, five, six, seven, eight, nine, ten or more fragrances different from Ethyl 4-oxopentanoate.
  • the fragrance composition represents a perfume oil.
  • Perfume oils usually comprise or consist of synthetic or natural (preferably) tasteless and odorless carrier oils which contain fragrances or fragrances (e.g. a specific plant) as artificial or natural substances in highly concentrated form (and optionally perfumery solvents and I or auxiliaries). Perfume oils are therefore often used for fragrance applications.
  • Perfume oils for example, are used to make perfumes by mixing them in (e.g. alcoholic) solutions which "entrain" the scents or fragrances when they evaporate and thus impart the sensory impression of a specific smell to the olfactory organ of the user, i.e. the human being.
  • Such mixtures can be, for example, a perfume, eau de perfume or eau de toilette.
  • Perfume oils are also used to produce a specific scent in living spaces, such as when used in fragrance lamps, atomizers or diffusers.
  • perfume oils can also be used in countless other articles or products.
  • the fragrance composition according to the invention comprises or consists of Ethyl 4-oxopentanoate and two or more fragrances different from Ethyl 4- oxopentanoate. More preferably, the fragrance composition according to the invention comprises or consists of Ethyl 4-oxopentanoate and three or more fragrances different from Ethyl 4-oxopentanoate. Most preferably, the fragrance composition according to the invention comprises or consists of Ethyl 4-oxopentanoate and four or more fragrances different from Ethyl 4-oxopentanoate.
  • Extracts from natural raw materials such as essential oils, concretes, absolutes, resins, resinoids, balsams, tinctures such as.
  • Ambergris tincture Amyris oil; Angelica seed oil; Angelica root oil; Anise oil; Valerian oil; Basil oil; tree moss absolute; bay oil; mugwort oil; benzoeresin; bergamot oil; Beeswax absolue; Birch tar oil; Bitter almond oil; Savory oil; Bucco leaf oil; Cabreuva oil; Cade oil; Calmus oil; Camphor oil; Cananga oil; Cardamom oil; Cascarilla oil; Cassia oil; Cassie-absolue; Castoreum-absolue; Cedar leaf oil; Cedarwood oil; Cistus oil; Citronella oil; Citron oil; Copaiva balsam; Copaiva balsam oil; Coriander oil; Costus root oil; Cumin oil; Cypress oil; Davana oil; Dill herb oil; Dill seed oil; Eau de brouts-Absolue; Oak moss absolute; Elemi oil; Tarragon oil; Eucalyptus citriodora oil; Eucal
  • Individual odorants from the group of hydrocarbons such as 3-carene; a- pinene; B-pinene; a-terpinene; y-terpinene; p-cymene; bisabolene; camphene; caryophyllene; cedrene; farnesene; limonene; longifolene; myrcene; ocimene; valencene; (E,Z)-1 ,3,5-undecatriene; styrene; diphenylmethane; of the aliphatic alcohols such as Hexanol; octanol; 3-octanol; 2,6-dimethylheptanol; 2- methyl-2-heptanol; 2-methyl-2-octanol; (E)-2-hexenol; 1 -octen-3-ol; mixture of 3,4,5,6,6-pentamethyl-3/4-hepten-2-
  • menthol isopulegol; alpha-terpineol; terpinenol-4; menthan-8-ol; menthan-1 -ol; menthan-7-ol; borneol; isoborneol; linalool oxide; nopol; cedrol; ambrinol; vetiverol; guaiaol; and their formates, acetates, propionates, isobutyrates, butyrates, isovalerianates, pentanoates, hexanoates, crotonates, tiglinates and 3-methyl-2-butenoates; of cyclic terpene aldehydes and ketones such as Menthone; isomenthone; 8- mercaptomenthan-3-or
  • Cineol cedryl methyl ether; cyclododecyl methyl ether;1 , 1 -dimethoxycyclododecane; (ethoxymethoxy)cyclo-dodecane; alpha-cedrene epoxide; 3a,6,6,9a-tetramethyldodecahydro-naphtho[2, 1 -b]furan; 3a-ethyl-6,6,9a- trimethyldodecahydronaphtho[2, 1 b]furan; 1 ,5,9-tri-methyl-13-oxabicyclo[10.
  • ester of cyclic alcohols such as 2-tert-butylcyclohexyl acetate; 4-tert-butylcyclohexyl acetate; 2-tert-pentylcyclohexyl acetate; 4-tert-pentylcyclohexyl acetate; 3,3, 5-tri methylcyclohexyl acetate; decahyd ro-2-naphthyl acetate; 2-cyclo-pentylcyclopentyl crotonate; 3-pentyl tetrahydro-2H-pyran-4-yl acetate; decahydro-2, 5, 5,8a- tetramethyl-2-naphthyl acetate; 4,7-methano-3a,4,5,6,7,7a-hexa-hydro-5, resp.
  • ester of cyclic alcohols such as 2-tert-butylcyclohexyl acetate; 4-tert-butylcyclo
  • 6- indenyl acetate 4,7-methano-3a,4,5,6,7,7a-hexahydro-5, or 6-indenyl propionate; 4,7- methano-3a,4,5,6,7,7a-hexahydro-5, or 6-indenyl isobutyrate; 4,7-methanooctahydro- 5, or 6-indenyl acetate; of esters of cycloaliphatic alcohols such as 1 -cyclohexylethyl crotonate; of esters of cycloaliphatic carboxylic acids, e.g.
  • 2-methyl-1 ,3-dioxolane-2-acetate 2-methyl-1 ,3-dioxolane-2-acetate; of araliphatic alcohols such as Benzyl alcohol; 2-phenylethanol; 1 -phenylethyl alcohol;
  • butyl- phenyl)propanal cinnamaldehyde; alpha-butylcinnamaldehyde; alpha- hexylcinnamaldehyde; 3-methyl-5-phenylpentanal; 4-methoxybenzaldehyde; 4- hydroxy-3-methoxybenzaldehyde; 4-hydroxy-3-ethoxybenzaldehyde; 3,4- methylenedioxybenzaldehyde; 3,4-dimethoxybenzaldehyde; 2-methyl-3-(4- methoxyphenyl)propanal; 2-methyl-3-(4-methylenedioxyphenyl)propanal; of aromatic and araliphatic ketones such as acetophenone; 4-methylacetophenone; 4- methoxyacetophenone; 4-tert.- butyl-2,6-dimethylaceto-phenone; 4-phenyl-2- butanone; 4-(4-hydroxyphenyl)-2-butanone; 1
  • butyl-1 1 -di-methyl-4-indanyl methyl ketone; 1 -[2,3-dihydro- 1 , 1 , 2, 6-tetramethyl-3-(1 -methylethyl) -1 H-5- indenyl]ethanone; 5',6',7',8'-tetrahydro-3',5',5',6',8',8'-hexamethyl-2-aceto-naphthone; of aromatic and araliphatic carboxylic acids and their esters, e.g.
  • the fragrance composition according to the invention is preferably, the fragrance composition according to the invention.
  • (a) is a mixture to reduce an odor
  • (b) is a mixture in which individual components, in use, develop an unpleasant odor which is reduced by the presence of Ethyl 4-oxopentanoate
  • (c) is a mixture in which one, two or more of the fragrances different from Ethyl 4- oxopentanoate have an unpleasant odor which is reduced by the presence of Ethyl 4- oxopentanoate.
  • said odor is an unpleasant odor selected from the group consisting of sweat, in particular human sweat, toilet odor, human faecal or urine odor, odors from faecal or urine from animals, kitchen odors, in particular odors of old fat, old fish or butyric acid, and smoke odor, in particular of cold smoke odor.
  • unpleasant odors can also be contained in such a mixture or develop during use.
  • composition according to the invention according to the first alternative (a) is a mixture for reducing an odor, in particular an unpleasant odor.
  • a mixture according to the invention which already comprises individual components which, when used, develop an unpleasant odor.
  • the purpose of the mixture according to the invention is to use Ethyl 4-oxopentanoate contained in such a mixture to reduce this developing unpleasant odor.
  • composition according to the invention which comprises one or more fragrances as described above, according to a preferred embodiment, is a mixture in which one, two or more of the fragrances contained in group (ii) already have an unpleasant odor; such an unpleasant odor is reduced by Ethyl 4-oxopentanoate to be used according to the invention.
  • the ratio of the total amount of Ethyl 4-oxopentanoate to the total amount of fragrances based on weight is in the range from 10: 1 to 1 : 50, preferably in the range from 5: 1 to 1 : 30, particularly preferably in the range from 2: 1 to 1 :20, particularly preferably in the range from 3:2 to 1 :10. Also for the purposes of this calculation, Ethyl 4-oxopentanoate is not considered as a fragrance.
  • the fragrances different from Ethyl 4-oxopentanoate are selected from the group consisting of:
  • compositions according to the invention comprising one or more of the preferred fragrances listed above, in particular in such cosmetic, body care, household and cleaning products, but in particular in such perfume oils according to the invention, the above statements on preferred weight ratios apply accordingly.
  • the total amount of Ethyl 4-oxopentanoate is preferably in the range from 0.01 to 10% by weight, preferably in the range from 0.025 to 5% by weight, particularly preferably in the range from 0.05 to 2% by weight, based in each case on the total weight of the composition.
  • the composition also comprises one, two, three or more auxiliaries called “application aids", selected from the group consisting of dipropylene glycol, diethyl phthalate, triethyl citrate, isopropyl myristate and benzyl benzoate.
  • application aids selected from the group consisting of dipropylene glycol, diethyl phthalate, triethyl citrate, isopropyl myristate and benzyl benzoate.
  • compositions according to the invention in particular perfume oils or other preferred compositions, comprise one, two, three or more application aids, preferably selected from the group of application aids described above, to achieve further improved effectiveness of the compounds of the formula (I) to be used according to the invention.
  • the fragrance composition comprises (a) one or more fragrances selected from the group consisting of:
  • a further aspect of the present invention relates to a preparation comprising the fragrance composition described above.
  • the preparation is selected from the group consisting of cosmetic, body care, household and cleaning products.
  • the preparation is selected from the group consisting of cleaning agents, air fresheners, textile hygiene products, body care products, hair care products, deodorants, antiperspirants and animal litter.
  • another product or object with an unpleasant odor can advantageously be perfumed or scented as desired, with the intensity of the unpleasant odor(s) being reduced and the unpleasant odor impressions (by humans) only being reduced or no longer be noticed.
  • Ethyl 4-oxopentanoate to be used according to the invention is adsorbed on a carrier which ensures both fine distribution of the compound in the product or in the preparation and controlled release during use.
  • Such carriers can be porous inorganic materials such as silica gels, zeolites, gypsum, clays, clay granules, aerated concrete, etc., or organic materials such as wood and cellulose-based substances.
  • Ethyl 4-oxopentanoate to be used according to the invention or corresponding mixtures can also be present in microencapsulated, spray-dried form, as inclusion complexes or as extrusion products and in this form a product, in particular a product to be improved in terms of smell by reducing an unpleasant odor or to be perfumed product to be added.
  • Microencapsulation of Ethyl 4-oxopentanoate to be used according to the invention can be carried out, for example, by the so-called coacervation process using capsule materials, e.g. made of polyurethane-like materials or soft gelatine.
  • Spray-dried Ethyl 4-oxopentanoate can be prepared, for example, by spraydrying a substance to be used according to the invention, i.e. an emulsion or dispersion is prepared, modified starches, proteins, dextrin and / or vegetable gums can be used as a carrier.
  • Ethyl 4-oxopentanoate to be used according to the invention or corresponding mixtures can be used in many preparations or products, they are preferably combined with one or more of the following auxiliaries or active ingredients: preservatives, abrasives, anti-acne agents, anti-aging agents, antibacterial agents, anti-cellulite agents, anti-dandruff agents, anti-inflammatory agents, anti-irritants, anti-irritants Agents, antimicrobial agents, antioxidants, astringents, antiperspirants, antiseptics, antistatic agents, binders, buffers, carrier materials, chelating agents, cell stimulants, cleansing agents, conditioning agents, depilatory agents, surfactants, deodorants, antiperspirants, emollients, emulsifiers, enzymes, essential Oils, fibers, fixatives, foaming agents, foam stabilizers, anti-foaming substances, foam boosters, fungicides, gelling agents, gelling agents, hair care
  • Preferred products or preparations are perfume extras, eau de perfumes, eau de toilettes, aftershaves, eau de colognes, pre-shave products, splash colognes and perfumed refreshing wipes and acidic, alkaline and neutral cleaning agents that are or are to be perfumed, such as e.g.
  • a preparation according to the invention or an article of daily use as described above contains one or more surface-active substances, preferably one or more surfactants and/or one or more emulsifiers.
  • Ethyl 4-oxopentanoate to be used according to the invention can be more easily incorporated into the indicated preparations or articles of daily use by means of surface-active substances.
  • Ethyl 4-oxopentanoate to be used according to the invention is preferably used in cosmetic, body care, household and cleaning products.
  • a preparation according to the invention selected from the group consisting of cleaning agents, air fresheners, textile hygiene products, body care products, hair care products, deodorants, antiperspirants and animal litter is particularly preferred.
  • Another aspect of the invention relates to a method for reducing odors, comprising or consisting of the following steps: mixing Ethyl 4-oxopentanoate with one or more, preferably two, three, four, five, six, seven, eight, nine, ten or more fragrances different from Ethyl 4-oxopentanoate
  • a mixture according to the invention which already comprises individual components which, when used, develop an unpleasant odor.
  • the purpose of the mixture according to the invention is to use Ethyl 4-oxopentanoate contained in such a mixture to reduce this developing unpleasant odor.
  • the method according to the invention also comprises reducing an unpleasant odor within a composition, which comprises one or more fragrances as described above, according to a preferred embodiment, is a mixture in which one, two or more of the fragrances contained in group (ii) already have an unpleasant odor; such an unpleasant odor is reduced by Ethyl 4-oxopentanoate to be used according to the invention.
  • the ratio of the total amount of Ethyl 4-oxopentanoate to the total amount of fragrances based on weight is in the range from 10: 1 to 1 : 50, preferably in the range from 5: 1 to 1 : 30, particularly preferably in the range from 2: 1 to 1 :20, particularly preferably in the range from 3:2 to 1 :10. Also for the purposes of this calculation, Ethyl 4-oxopentanoate is not considered as a fragrance.
  • the fragrances different from Ethyl 4-oxopentanoate is selected from the group consisting of: Alpha-hexyl cinnamon aldehyde, 2-phenoxyethylisobutyrate, dihydromyrcenol, methyl-dihydrojasmonate, 4, 6, 6, 7, 8, 8, -hexa methyl- 1,3, 4, 6,7,8- hexahydrocyclopenta[g]benzopyran, tetrahydrolinalool, benzyl acetate, 2-methyl-3-(4- tert.-butyl-phenyl)propanal, cinnamon alcohol, 1 -phenyl acetate, octahydro-2, 3,8,8, - tetramethyl-2-acetophenone, 2-acetyl-1,2,3,4,6,7,8-octahydro-2,3,8,8-tetramethyl naphthalene, 4-tert.-butylcycl
  • a method is relevant with which it can be assessed whether a particular substance is a suitable substance for a specific masking task, i.e. whether by use of this substance an (unpleasant) odor in the context of the present invention can be reduced.
  • a method is used to test the suitability of a test substance (N) comprising Ethyl 4-oxopentanoate for checking the reduction of an unpleasant odor, comprising the following steps: a) preparing or providing a malodor standard mixture (S) comprising or consisting of a substance having an unpleasant odor (M), i.e. a substance or a mixture, b) producing or providing a test mixture (T) also comprising the substance having an unpleasant odor (M) and the test substance (N), and c) comparison of malodor impressions of malodor standard mixture (S) and test mixture (T).
  • the test substance (N) and / or the test mixture (T) is a preparation according to the invention (as described above). Furthermore, it is therefore also preferred if the test substance (N) or the test mixture (T) in addition to Ethyl 4- oxopentanoate also comprises one or more fragrances. For the number and selection of the fragrances to be used, the statements made above apply accordingly. In the context of the method according to the invention, however, it is preferred if the test substance (N) itself contains no unpleasant-smelling (olfactory) substances.
  • the test method is carried out at a temperature of 20 ° C and a pressure of 1013 mbar. Accordingly, a method as described above is particularly preferred, wherein the comparison according to step c) is carried out at a temperature of 20 ° C and a pressure of 1013 mbar.
  • the steps a) or b) can be carried out under the reaction conditions mentioned.
  • the test substance (N) to be used according to the invention preferably also contains one or more fragrances, and more preferably optionally further auxiliaries or active substances (in particular those as described above).
  • more complex (olfactory) substance mixtures such as chords of fragrances and essential oils or perfume oils can be checked for their suitability for neutralizing or reducing odors, in particular unpleasant odors.
  • unpleasant odors used in the context of a method according to the invention, the comments made above apply accordingly.
  • a defined amount of an offensive smelling mixture i. a substance (M) is used. That is, preferably, the test method is performed so that the concentrations of the substance (M) in the malodor standard mixture (S) and the test mixture (T) are the same. This allows a particularly good comparison of the two mixtures.
  • test mixture comprising a substance (M) and a test substance (N) in comparison to other test mixtures and / or compared to the malodor standard mixture (S) in terms of their suitability for reducing an unpleasant odor (the substance (M)) is tested.
  • the malodor impression of the malodor standard mixture (S) and the test mixture (T) and preferably also the perfume or fragrance intensity of these mixtures is preferably evaluated in each case by 8 or more examiners (experts) by smelling in comparison to each other.
  • the malodor standard mixture (S) is assigned the intensity 6 in the most cases.
  • the examiners are chosen for their ability to reproducibly evaluate the strengths of odors.
  • the examiners are trained before the test series on the recognition of unpleasant odors and the reduction of unpleasant odors.
  • Ethyl 4-oxopentanoate to be used according to the invention has only a very slight inherent odor. Consequently, Ethyl 4- oxopentanoate can be used in any fragrance directions.
  • Example 1 Characteristics of ethyl 4-oxopentanoate
  • Ethyl 4-oxopentanoate can be produced from 4-Oxopentanoic acid/Levulinic acid by one of the procedures known in the literature.
  • Example 2.1 Selection and training of examiners
  • DPG odorless solvent
  • a bad smell in the context of the present text is an unpleasant odor in the sense of the definition mentioned above.
  • Test "A” multiple smelling strips (thin cardboard strips of an odorless paper) are dipped into a mixture comprising one or more malodors, i.e. comprising one or more substances, which cause an unpleasant odor impression (in humans).
  • DPG odorless
  • B. Selection Criterion 2 Examiners must be able to distinguish between different intensities or concentrations of bad smells or the corresponding substances mediating these odor impressions. For this purpose, samples of different concentrations of the respective bad smells are placed in a defined airspace. These samples are different malodor standard mixtures (S), which each contain a different concentration of a substance (M) with an unpleasant odor. Accordingly, these mixtures have different intensities of the respective bad smell and thus different intensive malodorous impressions. These samples are sorted by the examiner according to intensity (odor strength). The sequence of concentrations must be properly recognized and evaluated by the examiners. Examiners who have passed both tests (A, B) can take part in the raw material tests described below.
  • a test mixture (T) to be used in the present invention preferably comprises a substance (M) having an unpleasant odor and a test substance (N) in a sample container (e.g., a glass), but (M) and (N) are preferably not mixed with each other, but (as described above) coexist.
  • a sample (unperfumed and marked as such) with only bad odor (ie a malodor standard mixture) serves as a reference for the examiners.
  • a "non-perfumed sample” is a mixture comprising a substance (M) with an unpleasant odor, but not Ethyl 4-oxopentanoate to be used according to the invention or a corresponding mixture.
  • This sample is defined to a value that may vary depending on the type of bad smell, but is usually at "6”. All samples are preferably presented encoded. As a rule, at least one of the coded samples is empty (filter paper only) or provided with unperfumed bad smell (reference, as described above). This will further control the examiners and the results achieved.
  • Example 2.2 Test against sweat odor
  • Example 2.3 Test against toilet odor
  • Ethyl 4-oxopentanoate to be used according to the invention reduces the unpleasant toilet odor by 72 %.
  • Example 2.4 Test against kitchen odor [00103] From a solution (Substance (M) with an unpleasant odor) whose odor was mimicked by the smell of a commonly used kitchen consisting of fats, various bratwomen and an odorless solvent, 1 pl each was placed on a filter paper. 1 pl each of different substances to be tested (N) was also applied to filter paper and placed in a glass together with the odor sample. The samples were allowed to rest for 15 h. 8-12 examiners evaluated the samples for perfume / fragrance and kitchen odor intensity (malodorous impression). Indicated are the mean values from the individual ratings.
  • Ethyl 4-oxopentanoate to be used according to the invention reduces the unpleasant kitchen odor by 42 %.
  • Example 2.5 Test against smoke odor
  • Ethyl 4-oxopentanoate to be used according to the invention reduces the unpleasant smoke smell by 27.2 %.
  • Example 3 Use in combination with fragrances
  • EUCALYPTOL (1,3, 3-trimethyl-2-oxabicyclo [2.2.2] octane) 10 10
  • TERPENENOL-4 (4-methyl-1 - (1 -methylethyl) -3-cyclohexene-1 -ol) 1 1
  • MADRANOL ® (alpha-ethyl-2,2,6-trimethyl- (Z) -cyclohexanpropanol) 6 6
  • EUCALYPTOL (1,3, 3-trimethyl-2-oxabicyclo [2.2.2] octane) 0.6 0.6
  • PALISANDAL (1,1 -dimethoxycyclododecane) 4.5 4.5
  • ISOMUSCONE cyclohexadecanone
  • the mixtures A1, A2, B1 and B2 were also tested in 500 ml wide mouth bottles made of brown glass.
  • a sample (unperfumed and marked as such) with only bad odor (Malodor Standard Mixture (S)) serves as a reference for the examiners. This sample is defined to a value that may vary depending on the type of bad smell, but is usually at "6". All samples are preferably presented encoded.
  • At least one of the coded samples is empty (filter paper only) or provided with unperfumed bad smell (reference). Since complex perfume oils and blends usually have a stronger effect against unpleasant odors than individual chemicals, the blends are preferably tested in a less amount than the individual chemicals. [00112]
  • Example 3.1 Test of the mixtures A1 to B2 (A1, A2, B1, B2) against butyric acid odor
  • the mixture of the perfume oils A2 and B2 according to the invention leads to a particularly strong reduction of the (unpleasant) butyric acid odor.
  • Example 3.2 Test of the mixtures A1 to B2 against sweat odor
  • Example 3.3 Test of the mixtures A1 to B2 against smoke smell
  • the mixture of the perfume oil A2 or B2 according to the invention leads to a greater reduction of the unpleasant smoke odor than that of the perfume oil A1 or B1.
  • Example 4 Perfume oil with rose odor containing
  • Example 5 Perfume oil with white floral odor containing Ethyl 4-oxopentanoate
  • Vertocitral (2,4-dimethyl-3-cyclohexenecarboxaldehyde) 5.00
  • Methyl benzoate 10% in DPG 25,00 para-methylcresol, 10% in DPG 10.00 nerol 20.00 phenylpropyl 5.00
  • Example 6 Formulation and Application Examples in Finished Products
  • Example F1 Deodorant formulation in the form of a roll-on gel
  • Example F2 cream
  • Example F3 O / W Lotion
  • NAME Wt .-% paraffin oil 5.00 isopropyl palmitate 5.00
  • Example F4 air freshener in gel form
  • the resulting, preferably still warm mixture is poured into the desired shape (spheres, hemispheres, pillows, cylinders, cuboids, cubes, shells or the like).
  • the desired shape spheres, hemispheres, pillows, cylinders, cuboids, cubes, shells or the like.
  • an air freshener is obtained in gel form, the loading on Perfume oil from Example 5 is about 20 wt .-% based on the total weight of the air freshener.
  • Example F6 Foot cream
  • Example F7 Hairstylist
  • Example F8 Maintenance mask
  • Example F9 Skin oil
  • Example F11 Wet wipes
  • Present components are mixed to form a composition or mixture: 30 parts by weight of dipropylene glycol, 25 parts by weight of Ethyl 4-oxopentanoate, 15 parts by weight of isopropyl myristate; 15 parts by weight of triethyl citrate and 15 parts by weight of benzyl benzoate.
  • an emulsifier a 0.05% aqueous solution is prepared from this composition, with which wet wipes are treated.
  • the treated wipes smell much more neutral than untreated. This means that the typical unpleasan) smell of wet cardboard is no longer perceptible.
  • Example F12 Aerosol spray with effect against tobacco smoke odors on textiles
  • composition or mixture [00139] The following components are mixed to form a composition or mixture:
  • Example Fl 3 Aerosol spray with effect against kitchen odors on textiles
  • the following components are mixed to form a composition or mixture:
  • a water-based aerosol spray containing 1% by weight of this composition is sprayed on curtains or garments adhered to a strong kitchen smell of fried onions and hot frying fat. After spraying the curtains smell much more neutral, the unpleasant greasy, onion-like smell is no longer perceptible.
  • Example F14 Microcapsules having an effect against urine odor (e.g., in
  • composition or mixture [00143] The following components are mixed to form a composition or mixture:
  • Ethyl 4-oxopentanoate 25 parts by weight of Ethyl 4-oxopentanoate, 10 parts by weight of isomenthyl acetate, 20 parts by weight of isopropyl myristate, 30 parts by weight of triethyl citrate and 15 parts by weight of benzyl benzoate.
  • This composition is brought into a microencapsulated form (average particle size: 78 microns) with starch sodium octenylsuccinate (E 1450) and a sugar alcohol by spray drying so that the loading of the microcapsules on the composition indicated above is 50% by weight.
  • the microcapsules are placed between two paper layers glued to the edge and incorporated into a paper diaper. On contact with moisture, the odor-neutralizing composition is released and significantly reduces the appearance of urine odor compared to untreated diapers.
  • Example F15 Neutralization of Odor from unperfumed Washing Powder
  • compositions or mixture 20 parts by weight of dipropylene glycol, 25 parts by weight of Ethyl 4-oxopentanoate, 15 parts by weight of isopropyl myristate, 15 parts by weight of triethyl citrate, 5 parts by weight of benzyl benzoate and 20 parts by weight of a perfume oil containing 35% by weight of fragrances.
  • a 0.3 percent solution of this Composition is sprayed onto unperfumes washing powder. After spraying, the odor (of the washing powder) has become much more neutral, the greasy-rancid smell is no longer perceptible.
  • Example F16 Neutralization of toilet odor
  • Example F16.1 Artificial toilet odor
  • NAME Parts by weight dipropylene 62.82 skatol 0.91 beta-thionaphthol 0.91 mercaptoacetic 21.18 caproic 6.00 p-Kresylphenylacetat 2.18
  • composition or mixture [00150] The following components are mixed to form a composition or mixture:
  • the quality of the room air is evaluated by an expert panel after 30 minutes.
  • the odorreducing composition containing toilet sticks led to a significantly odor-neutral impression, the smell of the perfume oil was clearer and cleaner. Similar effects can be achieved with the odor-reducing composition and perfume oils of a flowery or citrusfresh type.
  • composition or mixture [00152] The following components are mixed to form a composition or mixture:
  • the quality of the room air is evaluated by an expert panel after 30 minutes.
  • the room air improvers containing the odor-reducing composition led to a significantly more neutral odor impression, and the odor impression of the perfume oil was clearer and cleaner.
  • Example F17 Reducing the odor of an unscented laundry softener
  • a laundry softener base prepared from 70 parts by weight demineralized water, 0.25 parts concentrated hydrochloric acid, 1 part calcium chloride dihydrate, 0.5 parts polysorbate 20, 27 parts Varisoft 315 (Witco) was mixed with 1.25 parts by weight of a perfume oil ( containing 44 wt .-% of fragrances other than Ethyl 4-oxopentanoate). By adding 0.15 parts by weight of Ethyl 4-oxopentanoate the odor of the finished product is much more neutral, the product smells altogether cleaner and fresher.
  • Example F18 Neutralization of cat urine (odor)
  • Example F19 underarm spray
  • composition or mixture [00158] The following components are mixed to form a composition or mixture:
  • a spray with the same composition is prepared, which contains no odor-reducing composition, but 1.2 parts by weight of perfume oil.
  • the spray with the odor-neutralizing composition reduces unpleasant odor significantly better and the fragrance of the perfume oil is perceived much more better.
  • Example F20 hair conditioner with UV protection Component INCI name wt wt
  • Example F21 Deodorant sticks NAME A B
  • Example F22 Microemulsion gels
  • Neo Helipan OS Ethylhexyl Salicylate, Symrise
  • Example. F24 Suspension Sticks NAME Wt .- Wt .- Wt .-
  • Triclosan® (5-chloro-2- (2, 4-dichlorophenoxy) phenol) 0.30 - 0.30
  • Ethylhexylglycerol 0.50 0.80 0.50
  • Example F25 Deodorant atomizer
  • PEG-40 hydrogenated castor oil 3.00 3.00 3.00 NAME Wt .- Wt .- Wt .-
  • Triclosan® (5-chloro-2- (2, 4-dichlorophenoxy) phenol) 0.25
  • Hydrogenated castor oil 5.00 5.00 beeswax 6.00 6.00
  • Neo Heliopan AV ethylhexyl methoxycinnamate, Symrise
  • Neo Heliopan 357 (butyl methoxydibenzoylmethane, Symrise) 1.00
  • Example F27 Deodorant pens
  • Triclosan® (5-chloro-2- (2, 4-dichlorophenoxy) phenol) 0.30
  • Example F28 Antiperspirant sticks
  • Phenyl Trimethicone (SilCare TM Silicone 15 M 50) 13.50 13.50 NAME Wt .- Wt .-
  • Cetiol CC (dicaprylyl carbonate) 13.50 13.50 stearic acid 3.50 3.50
  • PEG-8 distearate (Cithrol 4 DS) 4.10 4.10 petrolatum 6.90 6.90 aluminum chlorohydrate 13.80 13.80
  • Neo Heliopan Hydro ® Phenylbenzimidazole Sulfonic Acid, Symrise

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Abstract

L'Invention concerne l'utilisation de 4-oxopentanoate d'éthyle pour réduire les odeurs ou comme agent auxiliaire pour réduire les odeurs.
PCT/EP2022/057929 2022-03-25 2022-03-25 4-oxopentanoate d'éthyle pour réduire les odeurs WO2023179870A1 (fr)

Priority Applications (1)

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Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
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WO2023179870A1 true WO2023179870A1 (fr) 2023-09-28

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Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4719105A (en) 1975-11-05 1988-01-12 Bush Boake Allen, Inc. Method, compositions and compounds useful in room fresheners employing cyclohexyl alcohol and ester derivatives
EP2583696A2 (fr) * 2011-10-20 2013-04-24 International Flavors & Fragrances Inc. Agents contre les mauvaises odeurs de réactifs faiblement volatils et leurs procédés d'utilisation
EP3315031A1 (fr) * 2015-07-24 2018-05-02 Japan Tobacco, Inc. Composition
CN108244689A (zh) * 2017-12-12 2018-07-06 河南中烟工业有限责任公司 一种改善焦甜香叶组香气特征的香料模块配方及其在卷烟中的应用
US20180303109A1 (en) * 2015-10-30 2018-10-25 San-Ei Gen F.F.I., Inc. Dairy-product deterioration-odor masking agent and dairy-product deterioration-odor masking method

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4719105A (en) 1975-11-05 1988-01-12 Bush Boake Allen, Inc. Method, compositions and compounds useful in room fresheners employing cyclohexyl alcohol and ester derivatives
EP2583696A2 (fr) * 2011-10-20 2013-04-24 International Flavors & Fragrances Inc. Agents contre les mauvaises odeurs de réactifs faiblement volatils et leurs procédés d'utilisation
EP3315031A1 (fr) * 2015-07-24 2018-05-02 Japan Tobacco, Inc. Composition
US20180303109A1 (en) * 2015-10-30 2018-10-25 San-Ei Gen F.F.I., Inc. Dairy-product deterioration-odor masking agent and dairy-product deterioration-odor masking method
CN108244689A (zh) * 2017-12-12 2018-07-06 河南中烟工业有限责任公司 一种改善焦甜香叶组香气特征的香料模块配方及其在卷烟中的应用

Non-Patent Citations (2)

* Cited by examiner, † Cited by third party
Title
K. BAUER: "Common Fragrance and Flavor Materials", 2001, WILEY-VCH
S. ARCTANDER: "Perfume and Flavor Materials", vol. 1, 2, 1969

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